


To sleep: perchance to dream

by oftennot



Category: Critical Role (Web Series)
Genre: Angst, F/M, Friends With Benefits, Pining, Porn with Feelings, Unrequited Love, Vaginal Fingering, Vaginal Sex
Language: English
Status: Completed
Published: 2020-04-02
Updated: 2020-04-02
Packaged: 2021-02-28 17:27:46
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 1,861
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23440921
Author URL: https://archiveofourown.org/users/oftennot/pseuds/oftennot
Summary: In which Jester and Caleb having been sleeping together for some time, but Jester longs for more.
Relationships: Jester Lavorre/Caleb Widogast
Comments: 7
Kudos: 99





	To sleep: perchance to dream

.

.

_To be, or not to be: that is the question_

.

_Whether ’tis nobler in the mind to suffer_

.

_’Tis a consummation_

_Devoutly to be wish’d._

.

.

Jester knows well how to hide, how to move silently in the night, where to find the darkened corners and alcoves to disappear into, the places perfect for listening to all without being seen. From there she watched, eyes wide and flickering in the dim light of candles and chandeliers, the brush of fingertips on hands and shoulders, lips drawing closer to whisper sweet words into an ear, looks exchanged that expressed what words could not. Jester learned the myriad of ways lovers could dance around each other before falling into bed together. 

Jester knows well that love and sex are not the same, and one does not necessarily follow the other. Her mother, after all, has courted many bedfellows, but she only fell in love with one. The body, for as soft and vulnerable and easy to break as it may be, is still more easily managed than matters of the heart.

Jester did not know before that the world outside of the Chateau would be so different. The story books did not accurately depict reality. 

Caleb Widogast is not quite the dashing prince or rugged swordsman that are often featured in tales of romance and passion. He is quieter, more soft spoken. Caleb is a man of restraint, who acts only after much deliberation and due caution. Yet when he’s with her, a side of him emerges that Jester thinks no one else has seen. 

His hands, usually fiddling with string or flipping through the pages of a book, are insistent and firm on her breasts, her ass, her thighs. His touch sends little shivers of pleasure up her spine with every caress. Each time his lips meet her skin something inside herself slowly starts to come undone, like the hands of a clock ticking in reverse. The sound of their panting floods the space between them. Jester thinks Caleb is whispering in Zemnian as his lips trail down her neck and across her collarbone with the same reverence and intensity she’s seen him afford to only his spell books. He commits every freckle and scar littered across her skin to memory like arcane runes that hold the secrets of the universe.

It’s almost overwhelming to be the sole focus of his attention. His hands never stop giving, his lips take greedily of her, and his eyes are always on her. He watches, capturing each moan he draws from her—the movement of her breasts when she sucks in a breath and how she bites her lips when his fingers slide into her. Jester smiles, sighing in pleasure as he builds a steady pace. Caleb leans closer and she moans for him, gripping at his collar. She wants him to know how good he makes her feel, how she feels his touch on her even hours after they’ve separated. 

He inserts another finger and hastens his ministrations. The knowledge that the obscene noises and unmistakable wetness gathering on the inside of her thighs are from _her_ and that it’s _Caleb_ who has her up against the wall of her room makes the unraveling happening low in her belly quicken. The book he brought under the pretense of explaining to her some spell or other has been long forgotten. The clock _tick tick ticks_ away. 

He’s warm, and Jester can’t help but wonder if he hasn’t cast a spell with the way a fire blooms inside her. The flames catch and spread, engulfing her. Jester imagines steam rising from where their bodies are joined. When she cums from Caleb’s fingers, he lets her ride out the waves of her orgasm on him, gently slowing his hand. Little puffs of breath wash over her head as he takes in the sight of her. After her moans have quieted out into pleased hums he removes his fingers and uses the cum to lather his cock, already erect and waiting, with a quick few pumps. 

He enters her easily; Jester is still coming down from her first orgasm and the sight of Caleb fucking her while still fully dressed in his clothes and her panties have been shoved hastily aside sends a fresh wave of arousal through her. She wants to be closer to him, needs to feel him surrounding her. Her arms wrap around his neck, fingers tangling themselves in his hair. His hands glide up her thighs to grab her ass, lifting her higher up against the wall, the angle making it easier to fuck her. He groans into her neck when she grasps a handful of hair and pulls, thrusting deeper inside her in response. 

It’s a familiar rhythm between them, the feel of skin against skin, kisses that are long and slow and rob them of breath, the air full of moans and whimpers but precious few words exchanged. A sense of urgency always hangs heavy over their meetings together. A need to savor, to draw out this moment before it inevitably ends. 

When they first kissed it felt like surrender. The intensity and desire with which Caleb moved his lips against hers let Jester know that he had wanted this far longer than she. And yet, when she reaches for his hand to hold it in hers, he pulls away and runs it over her body instead. When she breaks their kiss and leans back to look into his eyes, wanting to see him fall apart in her arms, he ducks his head into the familiar crook of her neck and groans. Jester is left wanting _something_ more even as she feels her body clench around him and the pleasure build within her. 

Caleb presses his body against hers, allowing the wall to hold most of her weight. His hands travel up along her hips, giving a brief squeeze as he thrusts hard and deep. Jester throws her head back when he hits the perfect spot that makes her toes curl and her blood sing. She tugs insistently at his hair and he nips at her throat before relenting to her kiss. The heat grows, licking away at all that she is and everything else around her until Caleb is all she knows. It’s him, it’s him. It’s always been him. 

She’s gasping into his mouth and he fucks her faster. They’re both so close. She shifts her hips to guide him in deeper. Jester cums, her arms and legs wrapped around him and his mouth on hers and he’s inside her—it’s almost enough to drown out the steady tick of the clock hands as they wind down. Caleb follows her soon after, his forehead coming to rest on hers as he sighs and the tension flows out of his body. 

They stay there tangled around each other for a few precious moments. Jester counts backwards from ten in her head. Then, like clockwork, Caleb moves to extract himself from her embrace, taking care to lower her to the floor and make sure she has her footing before stepping back, putting a foot of space between them. His movements are quick and perfunctory as he cleans himself up with a spell and smooths out the wrinkles in his clothes. She is still and silent as she watches him. He doesn’t look at her until he’s gathered his books and spell components, patted all his pockets and holsters to confirm he has all his belongings, then meets her eyes. 

“I’ll take my leave now,” he says.

Her heart beats in time with the clock. _Tick. Tock._ “Okay.” 

“Goodnight Jester.” 

She scrambles for something to say, to magic up some further excuse to ask him to stay, to lie in bed with her—they don’t have to cuddle or even talk, he can read his books while she sketches in her journal—there’s more than enough room for two. Jester sucks in a breath and opens her mouth to speak.

Caleb's lips are downturned in a slight frown, and his eyes dart quickly to the door and back, a movement she would’ve missed if her gaze hadn’t been glued to him. The desire to be close and _together_ turns cold and chokes her, the words dying in her throat. Jester swallows them down, and two very different words spill forth. 

“Goodnight Caleb.”

He pauses, his blue eyes unblinking as he searches her face, hands hanging loosely at his sides. Jester wonders what he sees, if he can read her like one of his spell books, whether it would even make a difference if he could. The clock ticks on. Caleb nods curtly, then turns and makes for the door. Jester continues staring at the spot he’d previously been inhabiting, the sound of the door opening and closing echoing throughout her room. 

She walks over to her bed and tucks herself into the covers, uncaring that her sheets will need to be washed in the morning. There are no indents in the bed where he would lie—Caleb always leaves soon after their coupling. Sometimes she’ll wake to the scent of molasses and parchment lingering in the air. The soreness between her legs and the bites peppered across her neck and shoulders are small reassurances that she didn’t dream up the encounter the night before. 

Jester knows well how to make herself fade into the background and slip away undetected. She knows how to flutter her lashes and giggle in just the fashion to make people shake their heads at her antics and dismiss her, none the wiser to the way her smile drops and her eyes lower to the ground when they turn away. People see only that which she permits them. 

She wonders how Mama does it. How she meets and connects with so many people on an emotional and physical level and makes them fall in love with her, while her own heart stays under lock and key. Maybe it’s because she already gave her heart away long ago, to a man who took it and then never came back. 

Jester bites her lip to hold back a sob. 

She can’t even do that. Her heart is on her sleeve for Caleb to see and do with as he pleases, but he won’t accept it. At least if she had given her heart away she wouldn’t be able to feel. This is a fate much worse, to carry around the heavy burden of an unfulfilled love. It’s useless and painful, she knows, to continue on the way they are. She should stop seeing him like this. 

But her bed is so large, and the sheets so cold, and she now aches for Caleb in ways and in places that she didn’t know she could before. He’s left traces of himself all over her heart and body, like ink spilled upon a page. All she can do is love him harder, more earnestly, and hope that one day it will be enough. 

Her eyes slowly drift shut, and the rhythmic clicks of the clock cease. 

The room is silent.

.

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_To die, to sleep;_

_._

_._

**Author's Note:**

> Yes, I know that the most unrealistic thing of this whole scenario is Caleb being strong enough to hold Jester up against a wall to fuck her. But for the fic I made him not quite a string bean. Jester deserves it.


End file.
